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26260

Sigma-Aldrich

6-Chloropurine

≥95.0% (HPLC)

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About This Item

Empirical Formula (Hill Notation):
C5H3ClN4
CAS Number:
87-42-3
Molecular Weight:
154.56
Beilstein:
5774
EC Number:
201-745-6
MDL number:
MFCD00075825
UNSPSC Code:
12352100
PubChem Substance ID:
57648167
NACRES:
NA.22

Assay

≥95.0% (HPLC)

color

yellow-orange

mp

>300 °C (dec.) (lit.)

solubility

DMF: soluble 0.2 g/10 mL, clear, colorless to light greenish-yellow

SMILES string

Clc1ncnc2[nH]cnc12

InChI

1S/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)

InChI key

ZKBQDFAWXLTYKS-UHFFFAOYSA-N

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General description

The acid-catalyzed reaction of 6-chloropurine with 3,4-di-O-acetyl-D-xylal has been investigated.

Application

6-Chloropurine has been used in the preparation of:
  • 9-alkylpurines via alkylation with various substituted alkyl halides in DMSO
  • 6-succinoaminopurine

Quantity

λmax. 264 nm, mol. absorption 8700 (0.1 M HCl)

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

JAN Code

26260-1G-F:
26260-BULK-F:
26260-VAR-F:
26260-5G-F:
26260-25G-F:

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Certificates of Analysis (COA)

Lot/Batch Number
BCBD2401V
BCBD6123V
450822/1
436854/1
427782/1

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Synthesis of Potential Anticancer Agents. XXVI. The Alkylation of 6-Chloropurine2.
Montgomery JA and Temple Jr C.
Journal of the American Chemical Society, 83(3), 630-635 (1961)
Synthesis of 6-succinoaminopurine.
C E CARTER
The Journal of biological chemistry, 223(1), 139-146 (1956-11-01)
Heterocyclic N-glycosides-V: Synthesis of unsaturated N-glycosides from 6-chloropurine and derivatives of d-xylal and l-arabinal. A conformational NMR study.
Fuertes M, et al.
Tetrahedron, 26(20), 4823-4837 (1970)
Dong-Chao Wang et al.
Organic & biomolecular chemistry, 9(22), 7663-7666 (2011-09-22)
An efficient method for the synthesis of 6-alkyl or 6-aryl purines (nucleosides) was developed via nickel-catalyzed Negishi cross-couplings of 6-chloropurines and organozinc halides. The ligand-free process gave good to excellent isolated yields at room temperature.
A Bzowska et al.
Zeitschrift fur Naturforschung. C, Journal of biosciences, 54(12), 1055-1067 (2000-02-24)
The phase transfer method was applied to perform the nucleophilic substitution of 2,6-dichloropurines by modified arylalkyl alcohol or phenols. Since under these conditions only the 6-halogen is exchanged, this method gives 2-chloro-6-aryloxy- and 2-chloro-6-arylalkoxy-purines. 2-Chloro-6-benzylthiopurine was synthesized by alkylation of
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